BRPI0804121A2 - methods for the resolution of 4- [4- (dimethylamino) -1- (4'-fluoro-phenyl) -1-hydroxy-butyl] -3- (hydroxymethyl) -benzonitrile as a racemic or non-racemic mixture. of enanciomers in their isolated enanciomers and for the manufacture of escitalopram - Google Patents
methods for the resolution of 4- [4- (dimethylamino) -1- (4'-fluoro-phenyl) -1-hydroxy-butyl] -3- (hydroxymethyl) -benzonitrile as a racemic or non-racemic mixture. of enanciomers in their isolated enanciomers and for the manufacture of escitalopramInfo
- Publication number
- BRPI0804121A2 BRPI0804121A2 BRPI0804121-0A BRPI0804121A BRPI0804121A2 BR PI0804121 A2 BRPI0804121 A2 BR PI0804121A2 BR PI0804121 A BRPI0804121 A BR PI0804121A BR PI0804121 A2 BRPI0804121 A2 BR PI0804121A2
- Authority
- BR
- Brazil
- Prior art keywords
- enanciomers
- racemic
- hydroxy
- fluoro
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- RVGFHORHCHHPCZ-UHFFFAOYSA-N 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile;hydrobromide Chemical compound Br.C=1C=C(C#N)C=C(CO)C=1C(O)(CCCN(C)C)C1=CC=C(F)C=C1 RVGFHORHCHHPCZ-UHFFFAOYSA-N 0.000 title abstract 3
- WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 title abstract 2
- 229960004341 escitalopram Drugs 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 3
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical class C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
MéTODOS PARA A RESOLUçãO DE 4-[4-(DIMETIL-AMINO)-1-(4'-FLUORO-FENIL)- 1 -HIDRóXI-BUTIL] -3 -(HIDRóXI-METIL)-BENZONITRILA COMO UMA MISTURA RACêMICA OU NãO-RACêMICA DE ENANCIÈMEROS EM SEUS ENANCIÈMEROS ISOLADOS E PARA A MANUFATURA DE ESCITALOPRAM. Esta patente descreve um método para a resolução de 4-[4-(dimetil-amino)- 1 -(4'-fluoro-fenil)- 1 -hidróxi-butil] -3 -(hidróxi-metil)-benzonitrila como uma mistura racêmica ou não-racêmica de enanciómeros em seus enanciómeros isolados, o citado método compreendendo as etapas de fracionadamente cristalizar 4-[4-(dimetil-amino)- 1 -(4'-fluoro-fenil)- 1 -hidróxi-butil]-3-(hidróxi-metil)-benzonitrila como um sal com o (+)-(S,S) ou (R,R)-enanciómero de ácido O, O'-di-p-toluoil-tartárico em um sistema de solvente compreendendo 1 -propanol, etanol ou acetonitrila.METHODS FOR SOLVING 4- [4- (DIMETHYL-AMINO) -1- (4'-FLUORO-PHENYL) - 1-HYDROXY-butyl] -3- (HYDROXY-METHYL) -BENZONITRIL AS A RACEMIC OR NOT RACEMIC OF ENANCIEMEROS IN ITS ISOLATED ENANCIEMERS AND FOR MANUFACTURE OF ESCITALOPRAM. This patent describes a method for the resolution of 4- [4- (dimethylamino) -1- (4'-fluoro-phenyl) -1-hydroxy-butyl] -3- (hydroxymethyl) -benzonitrile as a mixture racemic or non-racemic of enanciomers in their isolated enanciomers, said method comprising the steps of fractionally crystallizing 4- [4- (dimethylamino) -1- (4'-fluoro-phenyl) -1-hydroxy-butyl] - 3- (hydroxymethyl) benzonitrile as a salt with the O, O'-di-p-toluoyl tartaric acid (+) - (S, S) or (R, R) -enanciomer in a solvent system comprising 1-propanol, ethanol or acetonitrile.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200701314 | 2007-09-11 | ||
| DKPA200701314 | 2007-09-11 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| BRPI0804121A2 true BRPI0804121A2 (en) | 2009-09-29 |
| BRPI0804121A8 BRPI0804121A8 (en) | 2021-04-13 |
| BRPI0804121B1 BRPI0804121B1 (en) | 2022-04-12 |
Family
ID=39735675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0804121-0A BRPI0804121B1 (en) | 2007-09-11 | 2008-09-11 | METHOD FOR THE RESOLUTION OF 4-[4-(DIMETHYL-AMINO)-1-(4'FLUORO-PHENYL)-1-HYDROXY-BUTYL]-3-(HYDROXY-METHYL)-BENZONITRILE AS A RACEMIC OR NON-RACEMIC MIXTURE OF ENANCIOMERS IN THEIR ISOLATED ENANCIOMERS |
Country Status (52)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1987016A1 (en) | 2005-07-27 | 2008-11-05 | Aurobindo Pharma Limited | An improved process for the preparation of escitalopram |
| CN102796065A (en) * | 2011-05-27 | 2012-11-28 | 江苏豪森医药集团连云港宏创医药有限公司 | Method for preparing high-optical-purity escitalopram |
| CN104119240A (en) * | 2013-04-23 | 2014-10-29 | 中国人民解放军军事医学科学院毒物药物研究所 | Preparation method for (S)-(-)-alpha-methylaminopropiophenone |
| CN103497145B (en) * | 2013-10-10 | 2016-01-27 | 南昌大学 | A kind of preparation technology of optical purity E2020 |
| CN104119248A (en) * | 2014-08-08 | 2014-10-29 | 广东东阳光药业有限公司 | The preparation method of S-citalopram |
| CN107074750B (en) | 2014-11-14 | 2022-03-25 | 浙江华海药业股份有限公司 | A kind of method for splitting citalopram intermediate 5-cyanodiol |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8814057D0 (en) * | 1988-06-14 | 1988-07-20 | Lundbeck & Co As H | New enantiomers & their isolation |
| AR034612A1 (en) | 2001-06-25 | 2004-03-03 | Lundbeck & Co As H | PROCESS FOR THE PREPARATION OF RACEMIC CITALOPRAM AND / OR OF THE S- OR R-CITALOPRAM THROUGH THE SEPARATION OF A MIXING OF R- AND S-CITALOPRAM |
| AR034759A1 (en) * | 2001-07-13 | 2004-03-17 | Lundbeck & Co As H | METHOD FOR THE PREPARATION OF ESCITALOPRAM |
| IS7239A (en) * | 2001-12-14 | 2004-04-29 | H. Lundbeck A/S | Process for the production of acitalopram |
| CA2511143C (en) | 2002-12-23 | 2011-06-28 | H. Lundbeck A/S | Preparation of racemic and/or s- or r-citalopram diols and their use for the preparation racemic and/or s- or r-citalopram |
| AU2003242990A1 (en) * | 2003-01-17 | 2004-08-13 | Pulla Reddy Muddasani | Processes for the preparation of escitalopram and its precursor |
| WO2005047274A1 (en) * | 2003-11-12 | 2005-05-26 | Dr. Reddy's Laboratories, Inc. | Preparation of escitalopram |
| EP1877394A1 (en) * | 2005-04-04 | 2008-01-16 | Jubilant Organosys Limited | Process for the preparation of escitalopram or its acid addition salts |
| EP1987016A1 (en) * | 2005-07-27 | 2008-11-05 | Aurobindo Pharma Limited | An improved process for the preparation of escitalopram |
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2008
- 2008-08-29 NZ NZ570884A patent/NZ570884A/en not_active IP Right Cessation
- 2008-08-29 FI FI20085807A patent/FI121570B/en not_active IP Right Cessation
- 2008-09-01 IE IE20080708A patent/IES20080708A2/en not_active IP Right Cessation
- 2008-09-01 GB GB0815773A patent/GB2448848B/en not_active Expired - Fee Related
- 2008-09-01 NO NO20083756A patent/NO20083756L/en unknown
- 2008-09-01 TW TW097133379A patent/TWI391383B/en active
- 2008-09-02 LV LVP-08-154A patent/LV13813B/en unknown
- 2008-09-02 IL IL193845A patent/IL193845A/en active IP Right Grant
- 2008-09-02 HR HR20080425A patent/HRP20080425A2/en not_active Application Discontinuation
- 2008-09-02 BG BG110206A patent/BG110206A/en unknown
- 2008-09-02 IS IS8758A patent/IS8758A/en unknown
- 2008-09-02 EA EA200801797A patent/EA012787B1/en not_active IP Right Cessation
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- 2008-09-04 CZ CZ20080537A patent/CZ2008537A3/en unknown
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- 2008-09-10 CO CO08095718A patent/CO6140012A1/en not_active Application Discontinuation
- 2008-09-10 UA UAU200901635U patent/UA41919U/en unknown
- 2008-09-10 ES ES08801398T patent/ES2368294T3/en active Active
- 2008-09-10 CN CNA2008101686272A patent/CN101386583A/en active Pending
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- 2008-09-10 PT PT08801398T patent/PT2061753E/en unknown
- 2008-09-10 SG SG200806650-8A patent/SG151195A1/en unknown
- 2008-09-10 EP EP11172640A patent/EP2397461A1/en not_active Withdrawn
- 2008-09-10 DE DE102008046530A patent/DE102008046530A1/en not_active Withdrawn
- 2008-09-10 CL CL2008002686A patent/CL2008002686A1/en unknown
- 2008-09-10 SI SI200830361T patent/SI2061753T1/en unknown
- 2008-09-10 DK DK08801398.2T patent/DK2061753T3/en active
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- 2008-09-10 WO PCT/DK2008/050222 patent/WO2009033488A1/en not_active Ceased
- 2008-09-10 PL PL08801398T patent/PL2061753T3/en unknown
- 2008-09-10 ES ES200802582A patent/ES2334875B1/en not_active Expired - Fee Related
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- 2008-09-10 FR FR0856077A patent/FR2920766A1/en active Pending
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- 2008-09-11 KR KR1020080090058A patent/KR101054224B1/en active Active
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- 2008-09-11 LU LU91479A patent/LU91479B1/en active
- 2008-09-11 TR TR2008/06903A patent/TR200806903A2/en unknown
- 2008-09-11 BR BRPI0804121-0A patent/BRPI0804121B1/en active IP Right Grant
- 2008-09-11 BE BE2008/0498A patent/BE1017548A6/en not_active IP Right Cessation
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2011
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2017
- 2017-06-26 AR ARP170101761A patent/AR108885A2/en unknown
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